Tell me about your early years and where you come from.

I was born at home in San Leandro, in the East Bay, just south of Oakland, so I’m a Bay Area native. I have three sisters who were also born at home, one older and two younger. I soon moved to Hayward where my parents still live now, and grew up going to the New Haven Unified School District because my mom taught there. And she taught everything from performing arts to working with kids at risk and is now doing dropout prevention. My dad is a doctor and his practice is in Fremont, so we’d commute from Hayward not too far to Union City.

I would say looking back now one of my formative things about my upbringing is that I’m mixed. I’m part Native American. San Carlos Apache from Arizona, Eastern Band Cherokee from the Carolinas, Hawaiian a couple generations but originally from Cebu, which are islands off the Philippines and Japanese from Osaka. And English, hence my last name. Apparently some bastard blood from King Henry V or something crazy like that. My aunt, I think, did a bunch of family trees but at some point, everyone connects back.

I think given that ethnically diverse background, my parents’ approach to raising us was grounded more in a common indigenousity, a common indigenous approach to simply having a connection to this earth and to this land. So we grew up farming our whole hillside. Everything from beans and corn that are way taller than me. Tomatoes and kale and all sorts of greens and squash. All different types of flowers and succulents. It’s still thriving to this day. Growing up, it was really annoying to go into the backyard and do all of our compost and create our own soil, but I got a chance to help build that little organic garden.

It was frustrating being out there in the backyard watering, when other kids are playing and I was always out there working. Though I think it did ground me and I still have a deep connection and sense of place on this earth. It also reinforced a farmer’s work ethic from my dad and his father who farmed on the eastern shore of Maryland. So there was definitely some influence from my dad and influence from my mom. She’s a performing artist so I have the analytical side from my dad and the creative side from my mom. While I was a baby, she took me around on tour and she would do different types of modern performances. Integrating dance, poetry, theater, and native influenced stories. My mom was just so generous with everyone. I remember growing up being so annoyed that we’d have people over to our house all the time. Staying at our place or coming over for brunch. She’d really try to take care of people and give as much to the local communities as possible. To this day she’s dropping off car loads of food, clothes and gifts for people all the time. When I was a kid I think I was annoyed but now I realize it had a much bigger impact on me in terms of my perspective on giving, even when you don’t think you have anything to give.

Where we lived was also interesting in the sense that we were in the foothills so our area really felt quite safe and unique. Every home was uniquely built. In one sense I felt secure in our middle-class lifestyle. But then on the other hand, near us or below us in the surrounding areas of where I went to school and other parts of Hayward and Oakland there was much more disparity.

So I felt like I got to see a pretty big spectrum growing up and then going into school in Union City. The elementary school I went to was in Decoto which had some notorious gangs and unfortunately some violence. So I think I was also exposed to that just walking around from daycare to school or staying after school.

I think I was super lucky as a kid. My parents put me in a Chinese preschool. I have a few vague memories of making Chinese symbols. So that was interesting. And then with kindergarten, there was a morning session and an afternoon session but my Mom was working at school so I just stuck around for both sessions. I think as early as first grade I started staying after school in math club with Mr. Fogel who was able to make a lot of things, even algebra, super accessible and fun. Using tactile blocks and objects. I think those things probably were also formative early on. It’s silly to me to even think about that because for most kids who go to amazing schools now that’s probably the norm. But for a public school with a big population of immigrants and English as a second language and super diverse minority school, I think those kind of after-school programs were unique.

Eventually I took a GATE test that put me onto a whole other track from elementary school all the way through high school. It’s pretty crazy to me to think that probably fundamentally altered my whole course. I was in 2nd grade but then I got moved to a 3rd grade class. And so, it just started accelerating from there to the honors track all the way through high school. The environment of those classes is very different than the other classes that were probably more chaotic. A lot crazier. With diversity of levels of knowledge and access. So, it’s crazy to me to think that things like that exist and hopefully they’re still getting funding. A lot of those kids went onto Berkeley. I was the only kid to go to Stanford out of a high school class of maybe 4000 plus students, which is unfortunate. I think more folks should have the ability to go there.

The other thing that probably shaped my perspective on how I operate now is that my parents didn’t take care of everything for me and hover. I don’t know what these things are called, hoverboard parents or helicopter parents [laughter].

Hoverboard parents!! It’s the 2016 version.

Yeah exactly. Rather than my mom making me lunch in the morning, I would make lunch for me and my mom and I don’t know if they were intentionally doing that or not, but that principle of empowering me, or putting the responsibility on me to take action extended throughout my life. So, for example, as there were a lot of Latino kids and a big Hispanic community in this Decoto area, I remember going out for the first time at recess and somehow being invited to play this ball game. I still have a couple of memories of how exhilarating that was and just cutting and kicking and having a great time. So that naturally inspired me to want to play more soccer. I went to my parents and told them I’d really love to play in a league. I was probably around seven or eight years old. They just told me to go and make it happen. And I’m like, uh, okay. So I remember being so annoyed as a kid that I would always have to fill out the release forms and apply for these things on my own. Not to say that they weren’t supportive once I started doing it because then they would come to all of my games and obviously drive me around and buy me gear. But they really wanted me to take that initiative and once I took that initiative they were super supportive.

The recess soccer games were another small thing that fundamentally changed my trajectory because from that point on, I just started playing more and more soccer. First with a local club, called the Patriots. That was my first team. Very patriotic. And then I just excelled and got invited to play with a select team. That coach was from Germany. Coach Burnett. And because he came from Germany he had such a better understanding of the fundamentals of the game than any American coach. The types of drills and discipline that we would have was just so much better than a lot of the other teams and we did pretty well for not having much in the way of resources. Eventually I was noticed by a wealthier club, Lamorinda, which is a club in Lafayette over the hills of Oakland as you go into Walnut Creek. It’s a very affluent area. I got noticed by that coach and they recruited me to play with them as Coach Burnett was beginning to wind down his team. So that also then exposed me to a whole other world of wealth. Just a whole other extreme than some of the kids that I went to school with. So I felt like I really got to see a pretty big spectrum of socio-economic status.

With that team we traveled to many places around the world. To Europe. To Barcelona in Spain multiple times. To Sweden multiple times. That wasn’t always easy. I remember having to fundraise from my parents’ friends and family. It wasn’t easy compared to the other teammates whose parents would just pay for them to go on these trips. But nevertheless, I think it really opened my eyes to different cultures, whether in South America or in Europe. I think that also fundamentally shifted my perspective. I remember being in Sweden, just amazed about how clean and how easy the public transportation system was and how friendly everybody was. I was just like, “Wow!” How beautiful the people were. It was amazing. I had such a good time there and continue to go back when I can.

The next big shift was playing in these tournaments like the Dallas Cup, that got me noticed by some coaches from Stanford. I started developing relationships with those folks. I got hurt in my senior year of high school. I hurt my lateral meniscus in a tournament. And so, that was right at the time when I was in conversations with recruiting, who encouraged me to apply. I had exceptional grades like most kids who first get into Stanford but what I could get from financial aid was actually bigger than what I could get from a scholarship to play soccer. I think soccer influenced me getting into Stanford, but I think that the academic merit also equally contributed to getting in, so that was a cool to start another trajectory.

It’s so interesting to me, how much exposure you had to both the lowest socioeconomic status in school and the highest socioeconomic status through soccer.

Yeah. Like some of the mansions, and private this and private that, [chuckles] to other people immigrating from Central America, or elsewhere and really having to struggle. And you have to learn how to hang with both.

I think I went through different phases in school. Wanting to be more cool and rebellious and wear baggy clothes and get into rap music. I definitely went through that phase. I definitely had my fair share of getting into trouble, whether it was pranks or doing things that we weren’t of age to be doing. There was a point before actually going to high school where I did get into a little trouble and I remember my parents picking me up at school and just crying and bawling. This is all while I’m getting straight A’s but I had this kind of dual personality of being exceptional in the classroom but also wanting to be cool with the cool kids and the influence of gangs and other sorts of stuff in schools. Anyways, I remember my parents just bawling and being so upset with me. It was the first time I realized that my actions have an impact on other people. So I think that was the big sort of ah-ha moment before going into high school. I just felt so grateful that I had that experience before it was too late. I thought, “Hey, I’ve got to be more responsible. I can’t just go along with some of these bad crowds. I’ve got to make decisions for myself and recognize that I have to take responsibility for my actions.” That was a huge turning point that helped keep me straight through high school because I didn’t want to have that type of experience again. I felt really lucky that it wasn’t anything that affected my record.

“There was a point before actually going to high school where I did get into a little trouble and I remember my parents picking me up at school and just crying and bawling. This is all while I’m getting straight A’s but I had this kind of dual personality of being exceptional in the classroom but also wanting to be cool with the cool kids and the influence of gangs and other sorts of stuff in schools. Anyways, I remember my parents just bawling and being so upset with me. It was the first time I realized that my actions have an impact on other people.”

Did you have any idea at that point what you wanted to be? Was there a specific point you became interested in design or technology?

It’s pretty crazy. I’d go to Stanford for occasional events like Native American Pow Wows. I’d been on the campus, but for whatever reason I thought that Stanford was just all doctors, lawyers, and business people. I was totally unaware of engineering or design as a track. I don’t even recall using the word design. I was definitely exposed to art and performing arts because of my sisters and my mom. But yeah, even today, to just realize that when you’re in the Valley and you think everyone knows about all this shit. Many kids around this area and in east bay probably don’t.

I would say also one other thing that influenced me and my three sisters was that my mom came from a lineage of really strong, independent women. My grandmother on my mom’s side, was a nurse and she raised them by herself single-handedly. With my great-grandmother, it’s kind of the same thing. In Arizona, she had her own home and was really independent. Horses and cattle and riding around. I think that matriarchy and having three sisters also shaped my values and perspective on gender. It has continued to play into some of the work that we do to this day. Investing in diversity. I think just having more respect for women. My dad was just more reserved and calm and zen-like. My mom was much more of the fiery one that would really take the initiative on things. So I think that’s also had an influence, but yeah, back to the question on how I got interested in design.

“I’d go to Stanford for occasional events like Native American Pow Wows. I’d been on the campus, but for whatever reason I thought that Stanford was just all doctors, lawyers, and business people. I was totally unaware of engineering or design as a track. I don’t even recall using the word design.”

So getting to Stanford was amazing. And with influence from my dad, I thought maybe I should go down the pre-med track. I started off with Human Biology, which is a really great major at Stanford that’s pretty interdisciplinary and I finished most of my pre-med requirements. From stuff in the lab to all the fundamentals. I also took a lot of courses at the medical school and that was when I started to realize that I wasn’t sure I wanted to be in these lab settings. It didn’t resonate as much with me.

At the same time too, that shit was kind of hard. I went from not studying ever to being with some of the best students in the world. So, I definitely remember being kind of shocked like, “Oh, wow!” I actually need to do some work here and at the same time playing division one soccer. That was challenging. I remember waking up super early for practice and after that I’d go to class. I would just be so tired. So sleepy and that was really challenging.

One of my teammates, Bronson McDonald was volunteering at this local non-profit called Mural Music & Arts Project in East Palo Alto. He was helping start their History Through Hip Hop program. He invited me to come out to some of the mural making that was going on at that time. That was the first time that I experienced research process like primary research, trying to figure out the local stories related to the theme like immigration which was a controversial theme at that time. Interviewing experts and local folks, and synthesizing all that. Getting everybody’s ideas out, and then visualizing it. That was the first time that I got exposed to the word design because that was a mural design process. So from the research to the design, to scale it on the wall, to unveiling it and having a big celebration.

That was when I first started having an awareness of the design process. It was just so powerful for me to spend time with local at risk youth which again is this conundrum in one of the wealthiest cities. All these resources and then to have a place so nearby where there’s so much disparity. It continued on this theme of having access to the folks at Stanford who are like princes and other crazy stuff, to folks that just don’t have the same level of privilege at all. Through the mural project I started to continue to volunteer and I started to realize, as they were applying for grants, there was this Community Technology Foundation of California (CTFC).

I looked around at my friends at Stanford. A lot of my friends didn’t go to East Palo Alto. They had no exposure to these stories. I’m like, is anybody actually going to come walk into the “ghetto” to look at some of these beautiful mural art pieces? And even if they do walk up to the wall, they’re not going to have a sense of all the stories and the meaning behind the wall. I thought what if we start putting these murals online? And started to think about a virtual mural tour. That’s when I started trying to apply the design process more to the web in software. I started hacking Google Maps which wasn’t open at the time and using different tools along with a couple of folks at the Mural Music and Arts Project like Zach Pogue and others. We pitched and got a grant to develop a project and document, digitally, many of the murals in the local Ravenswood City school district and up the peninsula to try to be able to expose these stories more digitally. That was the first web project that started to get me excited about the power of technology and power of software.

Concurrently I’d say one of my good friends from Stanford, Dan Greenberg, introduced me to Professor BJ Fogg at Stanford who’s done a lot around persuasive technology and how you can use technology for good. I ended up taking a Facebook class which is where I started to cross paths with Ben Blumenfeld, my co-founder at Designer Fund. That class was the first time that Facebook had opened up their platform for third party developers. Our objective was to build applications from scratch and launch them on the Facebook platform. We formed a small team. I basically worked on a status message app that has all the features that we kind of take for granted now, like embedding photos, linking, replies; that kind of stuff. Collectively with classmates who worked on a bunch of other projects, we got something like 10 million users in 10 weeks. Mainly making these spammy apps like hugs and kisses, but I think that had a huge impact on me because it was the first time I realized that we could have this mass interpersonal impact. I can’t think of another class in history that has reached that many people.

With the help of BJ, I started to do research in his lab on these mechanisms of how can you use social applications to get people to do good things. So, it really started to open my eyes to the power of software and that’s when I began to shift my courses into human computer interaction. I started to meet other people that were part of this small major at the time. It was inter-disciplinary between CS, linguistics, psychology and I started to take as many classes as I could in that track. That’s when I started to get more formal training in usability and user research. Around the same time at the end of that Facebook class, I presented my project and I got noticed by Chris O’Malley, who was at Venrock. Venrock is one of the oldest VC firms. They’ve invested in Apple. They’re from the lineage of Rockefeller money. He invited me to come on over, have lunch and meet the team. I didn’t have any awareness about venture capital, or really much about startups. Even though we did these kind of social apps. This is probably around 2008 or so. I worked in-house at Venrock with the senior designer and a couple of developers, and we would basically help build product for some of the companies that they were incubating. I spent most of my time with AskMeGo, which is a live questions and answer site. It was great. I got to help acquire a few hundred thousand users, similar to Aardvark which was acquired by Google. I worked on helping people get their questions answered and how to surface really good questions. That was a great first experience in tech.

So you joined Facebook Fund during college as well?

I then went back to grad school because I wanted to play for one more year. I got hurt one year at Stanford, so I wanted to play a 5th year of soccer, and I also wanted to keep going deeper into design. I lived off-campus and was biking down Lytton Ave in Palo Alto, near the old Techcrunch office and I ran into Dave McClure on the street, who I knew from the Facebook class. He was like, “Hey, what are you up to? Want to help work on this thing, Facebook Fund?” I was like, “That sounds cool,” but I just brushed it off. On top of everything that I was doing, playing soccer, taking super intense classes, then getting more into HCI, and doing research in the lab, I also worked most of the time, and paid my way through school.

One of the side jobs I had was at a high-end catering company that would do a lot of on-campus events. There was actually a VC related event that I was catering and I was learning about some of the start-ups and then I ran into Dave McClure again, and he was like, “Hey, man, you should probably come over and learn more and help out on Facebook Fund.” At that point I finally followed up, but I think it’s just crazy to me to think that you could have those kinds of serendipitous opportunities that are connections from class and you run into people on the street. The density of awesome people that you have access to is so easy to take for granted.

Then I joined Dave to help run design for “fbFund,” which was a joint venture between Facebook, Accel and Founders Fund. There were around 22 companies we invested in and I was responsible for running a small in-house design team to do short sprints with the portfolio companies around user acquisition, retention and revenue. It was amazing because I got to see all these companies in their infancy, when it was just a couple people around the table. Little companies like Zimride with Logan and John before they turned into the multi billion dollar company Lyft. Little companies like Run My Errand with Leah before she turned it into TaskRabbit. Alain and the Wildfire team before they grew it and sold it to Google for hundreds of millions. It’s crazy to see those companies form from the ground up.

“One of the side jobs I had was at a high-end catering company that would do a lot of on-campus events. There was actually a VC related event that I was catering and I was learning about some of the start-ups and then I ran into Dave McClure again, and he was like, ‘Hey, man, you should probably come over and learn more and help out on Facebook Fund.’ At that point I finally followed up, but I think it’s just crazy to me to think that you could have those kinds of serendipitous opportunities that are connections from class and you run into people on the street. The density of awesome people that you have access to is so easy to take for granted.”

Facebook wanted to have these companies build their products with “social” built into the product. Facebook Connect, the little button that you see around to log-in everywhere was new at the time, so they wanted more companies to showcase that. This is also when I started to realize that I needed to scale myself. I couldn’t serve all 22 companies. It wasn’t possible. So I started to think how could I take a lot of the learnings from the design school. How could I take a lot of that design thinking and prove that it works in the context of early stage start-ups. That includes office hours, talks, workshops, etc. I brought over whiteboards that I borrowed from the d.school. Scott Doorley who is now the Creative Director was so gracious to literally let me come with a truck and pick up a bunch of their equipment and take it over to Facebook. I had to figure out how to scale design and with the success of Facebook Fund, Dave went on to start his own fund.

As I was finishing up grad school, I was also starting to go deeper into design. I took a course, entrepreneurial design for extreme affordability. On one hand, I’m exposed to of all these social apps that are scaling and on the other end of the extreme, I’m working on low-cost water pumps, storage, and irrigation for rural farmers in Burma (Myanmar). It was a year long course where we did a lot of research, prototyping, testing, and went out to Burma during spring break. Being out in the field trying to empathize with people rather than just trying to push our solution onto them. Really trying to understand their needs. I remember sitting there in the field, observing this young girl, who was probably the same age as my sister at the time, a young teen, or maybe even younger, squat down and pick up gallons and gallons of water on her shoulder. She would go back and forth with tons of water over the course of a day. That’s one of the big things keeping her from going to school. I just had empathy for her. Especially given that I had a sister too, around her age. That again informed my perspective on what is meaningful impact. What’s the power of these technologies to really fundamentally affect people’s lives. I continued to do projects like that through grad school. For example in South Africa with FrontlineSMS:Medic. I worked on mobile texting apps to help virtual health workers report infectious diseases. Another amazing experience. That was another thing that opened my eyes to the power of technology to help. Walking into some of those hospitals and seeing people on stretchers. I think it grounded me in terms of technology that actually matters, that makes a difference, versus technology that just plays at our egos and our vices.

After finishing up grad school, I remember working harder during that time period, than ever. Of course, not sleeping, and all of the classic things. Anyway, 500 Startups didn’t have a brand, or even a name. We didn’t have a logo mark, or a typeface, or a website, or any money in the bank, or any space, or anything. The job, really, was just to do everything that I could, to help get 500 Startups off the ground. Launching our site, designing and helping close on 10,000 square feet in Mountain View, and doing that buildout. I really credit Dave, to just empower me. During my time there, I focused on our accelerator program and the problem of how to scale design services. How to scale great design, to dozens of companies at a time.

“I worked on mobile texting apps to help virtual health workers report infectious diseases. Another amazing experience. That was another thing that opened my eyes to the power of technology to help. Walking into some of those hospitals and seeing people on stretchers. I think it grounded me in terms of technology that actually matters, that makes a difference, versus technology that just plays at our egos and our vices.”

I experimented with everything. Design Sprints, talks, workshops, pattern libraries, UI kits, all sorts of things. It was great. I got to work with companies like Punchd, that was acquired by Google, and invested in Bēhance, which was acquired by Adobe. I worked with Tiny Post, acquired by Trip Advisor. I got a chance to not only help hands-on with companies, but also start to invest. One day while meditating at my place in Palo Alto, I just had this a-ha moment, which was like, shit, am I having long term impact with these companies? If I follow up, three, six months or a year down the road, how many of these companies will still be practicing these human-centered methods? What I noticed was that it was exponential decay. You would improve someone’s design sense, or their awareness of customers, but then if no one on the team was there to help sustain it, and to continue modeling and practicing these design behaviors, it’s not sustainable. People would just revert back to whatever they’re comfortable with. If you have an engineering background, you’re probably just going to focus more on solving problems from an engineering perspective, or a business perspective. It really bummed me out, that as I started to look back, I’m like, man, I’ve been working on all these companies over the past few years, but am I having long term impact with them?

In one of the books that I was reading at the time, Disrupt, or one of the conversations with John Lilly, the lesson was to do the opposite of what you’ve been doing. I was like, okay, I’ve been spending all of this time trying to make startups more design oriented. What if I do the opposite and help designers take the path of entrepreneurship with the thesis being if they get involved earlier on with great engineers and business people, they’ll increase the probability that they could make better designed products and services in the long run. That would also make my job a lot easier rather than trying to parachute in and solve people’s design problems. They would build that core competency in-house.

Simultaneously, Ben’s and my path crossed multiple times, at the Facebook class, Facebook Fund and we even collaborated on projects like peace.facebook.com. We kept in touch felt similar challenges and started to interview over 60 designers that we really respected and tried to understand why aren’t more designers taking this path of entrepreneurship. It kind of boiled down to lack of education, role models and capital. If you look at most of the most of the sources of capital, even going into schools, it’s primarily engineering based. When you look at professors and programs, they weren’t really preparing designers to start companies or to join companies early on. Or to be designers in the way that we expect them to be now. Every designer we spoke to was like, “Hey, if you try to solve this challenge, I’ll help you with time and/or money.” That was really encouraging. All these early conversations with influencers like Scott Belsky and others who said, “Yes, I’ll help.” I just remember thinking back, like, “Wow.” If those people didn’t say, “Yes I’ll help,” and want to pay it forward and give back to the design community, I don’t think that we would have continued on. That eventually led to Ben to take a sabbatical because he was maybe the fifth or sixth designer there and had been there for five or six years. He wanted to take a little break. We started going on hikes like Hidden Villa in Los Altos and then maybe working one day a week and then two days a week and then three, and it turned into all of our time trying to figure out how we can help more designers build businesses with meaningful impact.

Walk me through the decision to officially start Designer Fund.

It was around 2011 that we were doing the designer interviews. We felt like there was a real need to create a community of designers who were in tech who were building these companies from the ground up or joining early. At the same time, I felt, philosophically, that I wanted to work with less companies. I wanted to have more impact. That means, inherently, there’s just less companies that I can work with. With Dave’s blessing, I wanted to start to focus on Designer Fund full time. Over the course of 2011, I started to progressively decrease my time at 500 Startups and increase my time working on Designer Fund as an independent entity. I’m super lucky that Dave along with a number of other awesome investors were early supporters of Designer Fund. I’m super grateful to Dave McClure, Vinod Khosla, Jonathan Heiliger, Marc Andreessen, Eric Thomas, Shannon Callahan, Dave Morin, Chi-Hua Chien, Brandon Zeuner, Ryan Swagar, Marcus and Andrew Ogawa, John Lilly, Alex Diehl and many others. Folks that, I think, really just believed in the importance of creating an ecosystem and they saw the importance of design and were willing to support different educational events.

We then started giving grants to designers who were starting companies. For us it was an awesome way to give back to design community through free events, resources like our Designer Founders ebook, and through grants. As we moved into 2012, we started to formalize some of those things like writing larger grant check sizes and developing a better system for running different types of events. I think that’s when we even started with our first Women in Design event that Maria Molfino hosted. We went from mentorship programming to helping set up designers with formal advisorship positions with an equity stake. And also starting to operate as a band of angels where we’d help get our friends to co-invest in companies started by designers. We built on that momentum and then by 2013, we started to realize, “Wow, there’s a huge need need here.” Our inboxes were full of all these designers who are coming to us seeking support in one way or another, from funding, to transitioning to a new opportunity, to improving their career, and then all these companies were coming to us wanting to build their design teams, and so that led to the genesis of Bridge. We had all these great people coming to us but it was just Ben and I. We had to create some better way, a more scalable way of doing this. Previously I had built some internal tools with Kevin Xu, who’s now at Stripe, and the first version of a way for us to help process applications. We had all these applications for designers who wanted grants and so we thought maybe we can repurpose some of this technology to help us process all these applications from designers and all these applications from companies. That was also another big lesson for me, that some of the technology that you build early on, even if it’s scrappy MVP, really could accrue value over time and really magnify and scale your ability to serve people rather than just trying to do everything manually. That is obvious in retrospect. So we went from experiments in 2011 to formalizing events and grants in 2012 and then we launched Bridge and started angel investing in 2013.

Given our mission is to help designers build businesses with meaningful impact, one way of doing that is by helping designers build companies from the ground up as co-founders. What we soon realized was not every designer should be a co-founder, and actually, starting a company from scratch is hard as fuck. It’s so hard. At the same time there’s another path. Designers join existing companies that are doing well and on a growth trajectory. The next Facebook, the next Uber, etc. Joining one of those companies early on, arguably you could have just as much impact and you’re going to have a great experience learning. You’re going to meet a bunch of awesome designers and engineers. You might have a life-changing economic outcome, and just be in a better position to start a company yourself in the future.

On one hand, investing is great to help designers who are ready to be founders. Bridge, on the other hand, is about investing in future design leaders. It also related to our thesis that we believe that companies need to build design at their core. They can’t outsource it. It’s just like you don’t want to outsource your engineering, and great engineers attract other great engineers and so great designers attract other great designers. We felt strongly that helping build and educate design teams would bring a lot of value to companies and help accelerate the growth of designers.

When we launched Bridge, it was an experiment. We didn’t really know what was going to happen, so I just quickly worked with another designer and mocked up a site and worked on the positioning, but I didn’t spend a ton of time on it. I didn’t know if this was actually going to actually going to work. We partnered with some amazing photographers like you (Helena Price) and with the help of Laura Brunow-Miner and others to try to get perspective of a day in the life and what it’s like to be a designer at some of these top companies. Like Pinterest, Airbnb and Dropbox. Places that we felt truly value design. We’d meet the founders, we’d meet the design team. We’d check out the product. We’d make sure it’s a place where we would want to work ourselves because there’s just so much noise out there.

“We believe that companies need to build design at their core. They can’t outsource it. It’s just like you don’t want to outsource your engineering, and great engineers attract other great engineers and so great designers attract other great designers. We felt strongly that helping build and educate design teams would bring a lot of value to companies and help accelerate the growth of designers.”

And when we launched, it just got an overwhelmingly positive response. Way more demand from companies and designers than we could possibly fulfill. It was profitable since day one and we wanted to see if we could do it again. We ended up running another program that same year in 2013, in the Fall. Again we had amazing results of tons of designers applying, tons of companies wanting to participate. So then we realized that it wasn’t a fluke. Again in 2014 when we launched it again, Bridge 3, there was an amazing response. Our acceptance rate was tougher than Stanford or Harvard. We were really solving a need here for companies to help build and educate the design teams, to help designers accelerate their careers and hopefully become better designers and leaders.

And at the same time too, we started to get more and more companies coming to us seeking funding. They knew that we could actually add value and help build and educate design teams. There’s only so much that Ben and I can do as angel investors. There’s only so much we can do by calling up our friends to try to pool our money together to invest in them, so we thought, “Okay, I think we have enough data here that we’re ready to raise our first fund.” That was in 2014. We raised primarily from individual designers, great folks from some of the top companies around the valley, entrepreneurs, a couple of families, our own money and a few institutional funds. Now we’re managing over 20 million and we have a much clearer value proposition for people when they come knocking at our, we can say, “Hey, we can invest between $100K and a million dollars. Our average check size is $250K.” Ultimately we wanted to create a better experience for designer founders and designer entrepreneurs we wanted to partner with.

That was 2014. I think looking back, I don’t think we looked like anything else at the time. I don’t think there was any fund that was focused on design. There was no fund that also had this professional development program that was generating revenue and being profitable and had this community of designers. We just looked very unique, I think. Very different compared to the classic fund approaches. We wanted to build this ecosystem. Ben and I aren’t MBAs or coming from stereotypical investors wearing khakis and a button up shirt every day and vests and stuff. I think people were pretty surprised. I don’t think I was aware at the time, so it’s only looking back that I realize there’s not many diverse investors out there. Certainly not at the time from these different design backgrounds. Not at the time from an ethnicity perspective. I just met with a friend recently who told me that he’s been doing some research and there’s only about 30 general partners out there who are Hispanic and I was like, “Uhhhh, oh, okay.’ I didn’t even know that at the time. So if I factor that stuff in, probably the odds weren’t in our favor. We just didn’t have a long investment track record. We didn’t have a traditional background. Didn’t have what people who invest in funds would traditionally look for so thinking back I’m super grateful for all the folks like our advisor, Steve Vassallo, who took a chance on us and believed in our mission and believed in our approach.

“Ben and I aren’t MBAs or coming from stereotypical investors wearing khakis and a button up shirt every day and vests and stuff. I think people were pretty surprised. I don’t think I was aware at the time, so it’s only looking back that I realize there’s not many diverse investors out there. Certainly not at the time from these different design backgrounds. Not at the time from an ethnicity perspective.”

I guess what I’m trying to say is, each of those steps along the way from Venrock, to Facebook Fund, to 500 Startups to Designer Fund was uncomfortable. It was a stretch. It was almost that beginners naïvety. Looking back I don’t even know if I would do it again. Looking back it just doesn’t line up with what the norms at the time.

There were a lot of sacrifices too. Ben and I didn’t really pay ourselves. So many nights just working at our dinner table and doing all the classic stuff that I think any start up needs to do. Being super frugal, doing everything that we can to find alternative streams of revenue, engaging our community and a volunteer base. So scrappy. Doing events and getting sponsors and if it wasn’t for them I don’t know if I would pay rent that month. Just all the things that I think any entrepreneur would have to do. Seeing your bank account at zero or negative. In that way I think it was really great for Ben and I to have that deep empathy with all the companies that we invest in. I think it’s important never to lose sight of the struggle.

There’s all this hype that’s going right now and all these folks flocking to Silicon Valley maybe for the wrong reasons. It’s not a lottery ticket. Whereas for us, I don’t think we really ever wanted to be investors just for the sake of being investors. We felt that by investing, we could have a long-term impact with these companies. We could have an equity stake and be long term partners versus just consulting and parachuting in.

“There were a lot of sacrifices too. Ben and I didn’t really pay ourselves. So many nights just working at our dinner table and doing all the classic stuff that I think any start up needs to do. Being super frugal, doing everything that we can to find alternative streams of revenue, engaging our community and a volunteer base. So scrappy. Doing events and getting sponsors and if it wasn’t for them I don’t know if I would pay rent that month. Just all the things that I think any entrepreneur would have to do. Seeing your bank account at zero or negative. In that way I think it was really great for Ben and I to have that deep empathy with all the companies that we invest in. I think it’s important never to lose sight of the struggle.”

For example we have a poster from Facebook’s hacker way. “We don’t build products to make money, we make money so that we can build better products.” I think that’s always resonated with us. Where investing is not an end for us. It’s a means for, again, having meaningful impact and ultimately we want better designed products and services in the world. When we say better design, I think of that in a holistic sense. I think of that as an opportunity to impact someone’s life at a really deep level, and the opportunity to have breadth and scale across their life and across the globe. Of course we want to make a ton of money and generate great returns, but we think we can do that in a way that is aligned with our values.

“we have a poster from Facebook’s hacker way. “We don’t build products to make money, we make money so that we can build better products.” I think that’s always resonated with us. Where investing is not an end for us. It’s a means for, again, having meaningful impact and ultimately we want better designed products and services in the world. When we say better design, I think of that in a holistic sense. I think of that as an opportunity to impact someone’s life at a really deep level, and the opportunity to have breadth and scale across their life and across the globe. Of course we want to make a ton of money and generate great returns, but we think we can do that in a way that is aligned with our values.”

Since closing our first fund in 2014, we’ve been able to invest into some really great companies. Our largest investment is in Stripe, the global payments platform that’s really empowering commerce and online payments around the world. They’re now allowing anyone to set up US businesses and get that off the ground, it’s just amazing. Another one of our portfolio companies, ZenPayroll which is now re-branded as Gusto, is helping all these small business owners across the country, many not in tech, run their payroll. That’s really the backbone of the American economy, small businesses. We’re also investors in companies like Omada Health, which spun out of IDEO’s health practice. They help prevent people from getting diabetes, which then saves employers money and makes health plans more efficient. It’s like everybody wins. Individuals, the company, society. I just wish I could find ten more of those types of companies in all these different sectors that have, traditionally, been underserved from a user experience standpoint like financial services, education, health, business tools, creative tools. Over time I think we’ve been really blessed and fortunate to have lots of great people around the table to support Ben and I. An approach that we’ve always taken is that we’ve always surrounded ourselves with people that are amazing at what they do. When we first closed our fund, before even starting to invest, I think we interviewed maybe two dozen top investors that we respected and got perspective on what they thought worked and what didn’t work. We’re constantly practicing our own design process on ourselves and on our own business. We’re not just preaching design. We’re actually being hands-on and making our own tools, making our own site, doing a lot of our own stuff. Branding for example. I think it’s important to not lose sight of that. We primarily have been focused on just building, helping our companies and letting the work speak for itself, because I think you just see how there’s so much noise out there. We prefer to focus on the fundamentals of building a product that really solves a consumer’s pain point and need.

So, I have a question. In another interview, the idea was brought up that people tend to invest in what they know, and the problems that they can relate to. From your perspective, with your upbringing and being exposed to so many different socioeconomic backgrounds and cultures and not coming from the Silicon Valley pedigree—how does that affect you and what you choose to invest your time and money in?

I think there’s a number of companies that we’ve invested, for example ZenPayroll, which is now Gusto. We felt the pain of trying set up our own payroll, and file taxes, and all this back end office stuff. It’s like the last thing that we want to do with, especially when you’re really small. So I think in those cases, we felt that pain. Even creating our free resources like our Designer Founder’s e-book. We used Stripe to process payments. We used some of those tools ourselves as users and that’s one of the things whenever we look at a company—whether or not we’re the target user or not—we really try to use the product, and really dig into all the interactions. Which I think it’s pretty surprising how often most investors don’t do that.

Most investors aren’t really product focused and don’t really use the product which continues to surprise us. That’s okay, everyone has a different approach. When you start to dig into a product and start to put yourselves in the shoes of the user, even if we’re not deeply familiar with the problem, we can still try to put ourselves in their shoes and experience what that company is building. I think our ability to empathize with folks who are different than us allows us to imagine how a product or service could really impact someone’s life, hopefully for good.

“Most investors aren’t really product focused and don’t really use the product which continues to surprise us.”

Of course there’s some things like design tools, for example, like Framer Studio. We invested in them, and it’s like, “Yeah, we totally understand the need to prototype mobile web apps with code. With live data where you can make one change really easily and propagate that to a bunch of other things versus static mockups. We totally get that we’re moving towards a world where we need to build interactive prototypes. Some things like that, it’s really obvious for us to be able to have a point of view on. But then there’s other things where we’re actively looking for things that are outside our comfort zone. What are those areas that are traditionally underserved from a user experience standpoint? What are the industries with old, dinosaur incumbents that don’t really care about the user and just take advantage of them? Insurance, for example. They win based off of advertising campaigns, not on product and not by the user experience. I think there’s so many opportunities like that where because we are naturally curious, we’re going to go explore those spaces even if we don’t intimately know them or have experienced them.

“We’re actively looking for things that are outside our comfort zone. What are those areas that are traditionally underserved from a user experience standpoint? What are the industries with old, dinosaur incumbents that don’t really care about the user and just take advantage of them?”

I think in that sense, we actually like when we come across something that we don’t know a lot about initially, and then we have a whole research process. We bring in experts to help us. I’m actually looking for those opportunities where it’s going to be outside of my comfort zone because that’s where design could have the biggest delta or the biggest impact. Of course I’m going to look for the stuff that I know already is obvious. But the non-obvious things are going to be the most exciting things for us. Back to the example with Omada Health. My grandmother and great-grandmother have diabetes. So I remember seeing those needles, and just how horrible that process is. I know that my mom and others are at risk of being diabetic and that I actually was able to get her to go through the Prevent program at Omada, and lose ten pounds so I could see the impact that it was having in my personal life. That being said, we’re still open to finding more opportunities, whether it’s in mental health or other chronic illnesses, that just are totally preventable and with the help of technology we can accelerate prevention. I hope that in the future, we’ll be able to have more alignment with the health industry and the government to be able to even prescribe some of these digital therapeutic technologies.

My last question for you would be, just based on the lessons that you’ve learned, what advice would you have for young entrepreneurs or designers just getting started out in this industry?

One lesson is finding the right partner with complementary skills. Ben and I have really complementary paths. Me going through more of a Stanford HCI and research approach and Ben coming from UCLA with a formalized visual and graphic design approach. Me coming from early stage startups through venture capital firms and Ben coming through the rocket ship of Facebook, one of the most successful tech companies of our time. Another lesson is don’t underestimate the importance of finding a great opportunity. Just finding a company, a brand where you can learn a ton at, make a bunch of relationships with great engineers, designers, expand your network, and get exposed to what it takes to build a great product and scale it. If you get exposure to that early on it’s going to set you up for so much more in the future.

I want more designers to start companies. But I don’t think that’s always the right path for a lot of people. I think by joining an existing company right before that inflection point of growth, I think there’s a lot of benefit to doing that and I think you’re going to set yourself up to be in better position if you want to start a company in the future. There’s going to be exceptions and people like Joe and Brian who started Airbnb. They came from a very non-traditional route. Joe being an entrepreneur and Brian working at a design consultancy. It’s totally possible to start something when you don’t look qualified. You don’t look like any of the other teams that most investors look at. That’s totally possible but I think those guys were naturally entrepreneurial. If you are going to go that path to entrepreneurship, then I think it’s so important that you find a partner. For me I found Ben. Using the example of Joe and Brian, Airbnb wouldn’t be possible without their technical founder Nate. It’s so important to find both a design and engineering partner in that early team. I think that’s arguably more important than anything else at those early stages. To summarize, join a successful brand while it’s on its upward trajectory and learn everything you can while you’re there. Or if you are going to start something, really make sure you’re partnering with someone that you can make a long-term commitment to. Like Ben and I have made a minimum 10 year commitment to our mission and to each other. If you can’t make that type of commitment to someone, then maybe reconsider whether or not you want to get married and start a company together. [chuckles]

“Don’t underestimate the importance of finding a great opportunity. Just finding a company, a brand where you can learn a ton at, make a bunch of relationships with great engineers, designers, expand your network, and get exposed to what it takes to build a great product and scale it. If you get exposure to that early on it’s going to set you up for so much more in the future.”